Apiin

Apiin

IUPAC name 7-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one
Other names Apioside Apigenin-7-apioglucoside Apigenin-7-O-apioglucoside
Identifiers
CAS number	26544-34-3^N
PubChem	5280746
ChemSpider	4444321^Y
ChEBI	CHEBI:15932^Y
Jmol-3D images	Image 1
SMILES O=C\4c5c(O)cc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@@H]1OC[C@](O)(CO)[C@H]1O)cc5O/C(c3ccc(O)cc3)=C/4
InChI InChI=1S/C26H28O14/c27-8-18-20(32)21(33)22(40-25-23(34)26(35,9-28)10-36-25)24(39-18)37-13-5-14(30)19-15(31)7-16(38-17(19)6-13)11-1-3-12(29)4-2-11/h1-7,18,20-25,27-30,32-35H,8-10H2/t18-,20-,21+,22-,23+,24-,25+,26-/m1/s1^Y Key: NTDLXWMIWOECHG-YRCFQSNFSA-N^Y
Properties
Molecular formula	C₂₆H₂₈O₁₄
Molar mass	564.49 g/mol
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Apiin is a chemical compound isolated from parsley^[1] and celery. The aglycone of apiin is apigenin.

References

^ Bioavailability of Apigenin from Apiin-Rich Parsley in Humans
Hellen Meyer, Adrian Bolarinwa, Guenther Wolfram and Jakob Linseisen, Ann Nutr Metab, 2006, 50, pages 167-172, doi:10.1159/000090736

Flavones and their conjugates

Aglycones

Monohydroxyflavone	6-Hydroxyflavone

Dihydroxyflavones	Chrysin (5,7-dihydroxyflavone) 4',7-Dihydroxyflavone

Trihydroxyflavones	Apigenin (5,7,4'-trihydroxyflavone) Baicalein (5,6,7-trihydroxyflavone) Norwogonin (5,7,8-Trihydroxyflavone)

Tetrahydroxyflavones	Isoscutellarein (5,7,8,4'-Tetrahydroxyflavone or 8-Hydroxyapigenin) Luteolin (3',4',5,7-Tetrahydroxyflavone) Norartocarpetin (2',4',5,7-Tetrahydroxyflavone) Scutellarein (5,6,7,4'-Tetrahydroxyflavone)

Pentahydroxyflavones	Hypolaetin (8-Hydroxyluteolin) Tricetin (5,7,3',4',5'-Pentahydroxyflavone)

O-methylated flavones	Acacetin (Apigenin 4'-methyl ether) Artocarpetin (Norartocarpetin 7-methyl ether) Diosmetin (Luteolin 4'-methyl ether) Eupatilin (5,7-Dihydroxy-3',4',6-trimethoxyflavone) Genkwanin (Apigenin 7-methyl ether) Nepetin (Luteolin 6-methyl ether) Nobiletin (3',4',5,6,7,8-Hexamethoxyflavone) Oroxylin A (Baicalein 6-methyl ether) Pratol (7-Hydroxy-4-methoxyflavone) Sinensetin (3',4',5,6,7-Pentamethoxyflavone) Tangeritin (4',5,6,7,8-Pentamethoxyflavone) Techtochrysin (Chrysin 7-methyl ether) Tricin (Tricetin 3',5'-dimethyl ether) Wogonin (Norwogonin 8-methyl ether)

of apigenin	Apiin (Apigenin-7-O-apioglucoside) Apigetrin (Apigenin 7-O-glucoside) Isovitexin (Apigenin 6-C-glucoside) Rhoifolin (Apigenin 7-O-neohesperidoside) Saponarin (Isovitexin-7-O-glucoside) Schaftoside (Apigenin 6-C-glucoside 8-C-arabinoside) Vicenin-2 (Apigenin 6,8-di-C-glucoside) Vitexin (Apigenin-8-C-glucoside)

of baicalein	Baicalin (Baicalein 7-O-glucuronide) Tetuin (Baicalein 6-O-glucoside)

of hypolaetin	Hypolaetin 8-glucoside Hypolaetin 8-glucuronide

of luteolin	Cynaroside (Luteolin 7-O-glucoside) Isoorientin (Luteolin 6-C-glucoside) Orientin (Luteolin 8-C-glucoside) Veronicastroside (Luteolin 7-O-neohesperidoside)

Giraldiin A (4',5,5',7-Tetrahydroxy-3-methoxy-3'-O-α-L-arabinopyranosyloxyflavone) and B (5,5',7'-Trihydroxy-2',3-dimethoxy-4'-O-β-D-glucopyranosyloxyflavone)
Nepitrin (Nepetin 7-O-glucoside)
Oroxindin (Wogonin 7-O-glucuronide)
Scutellarin (Scutellarein 7-O-glucuronide)

Acetylated

Sulfated glycosides

Theograndin I (sulfated glucuronide of isoscutellarein) and II

Polymers

Synthetic

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